Last year, the booklists weren't completely finalized until the first day of class--one professor didn't actually bring his required texts into the bookstore, and we had to purchase them from a third-party seller during class. There's also an LSA used textbook sale that usually runs the first week (or so) of classes.
It's kind of bushleague from a "I'd like to know how much money I need" perspective, but it's generally good practice to hear what books are required versus those that merely supplemental.
Even if the booklist appears firm, I would highly suggest waiting. It didn't hinder me at all--outside of the constitutional textbook selling out of the bookstore and taking almost a month and a half to come in.
Also, as a quick note on supplemental texts: I purchased most of them. A couple were helpful, a couple didn't even get cracked. They were pretty much all available on reserve at the library. As such, I wouldn't buy them, if I was doing it all over again.

I would echo the above points regarding your GPA and LSAT. It is very difficult to gauge anything before you have any hard numbers.
A Sask connection (anecdotally) appears to be very important to the adcomm's decision--barring very strong GPA/LSAT. Now, that's not to say it would elevate an otherwise non-competitive application, but all things being "equal"...
My understanding is that before the Sask connection was implemented, they had a number of students who would transfer-out of USask following 1L. As such, they're more or less trying to gauge interest in staying for the entirety of law school. In addition, they want students who want to serve the Saskatchewan community, including the rural areas. I confirmed this with a faculty member over a beer last year--although, the second reason isn't as important as the first (USask has very strong representation in Alberta, and some graduates do end up in Toronto and Vancouver).
With that, your Sask connection would likely be considered quite strong. Good luck with the rest of your undergrad and your LSAT.

Agreed on a laser printer. Best pre-law school purchase I made. I absolutely loathe reading and noting-up cases (or anything, for that matter) on a computer though--I'm almost certainly strange in that regard.

Don't go to U of C, but born and raised in Calgary, so I can comment to some extent.
They're fairly comparable areas in terms of price. Both are fairly "trendy" areas with a lot of amenities.
Kensginton however is on the North side of the city, so you won't have to traverse downtown to get to the university--granted, this is isn't a huge deal outside of rush hour. That said, the Sunnyside train station (in Kensington) is three stops away from the U of C. I know you said transportation isn't a problem--which is important in a sprawling city like Calgary--but if you don't have to drive every day to and from school, you'll save a good chunk of cash on parking and gas.
I can't speak to individual buildings, unfortunately.

We were told explicitly within the first week of classes that if using Mac, turn off auto update, and don't update within a month of exams. I followed the advice and never had a crash. I know a few people who had examsoft crash (but anecdotally, it didn't seem isolated to Mac vs. PC).
The biggest issue I had with examsoft was a small lag between typing and the text showing on screen during some of the more typing-intensive exams. Doesn't sound like much, but it's pretty vexing when you're typing like a demon trying to get a question on qualified and future estates sufficiently answered. No idea if that's a common issue, or a "my Mac" specific issue though.

Even if someone were to say "it's not that important given your stats", wouldn't it be in your interest to put your best foot forward and write the best possible personal statement you can? After all, this is your only opportunity to really make your case directly to the adcomm in writing.

There was the above thread on this a few weeks back on the Windsor board. I was interested because I wondered the same thing. I think generally, it appears as though working during 1L is do-able, but (as you note) it becomes a personal time-management issue. The most salient advice that I noted on that thread was (assuming it's financially possible) to wait at least until second semester 1L. Now sure, there are possible issues with that (such as potentially leaving Saskatoon in the summer--I'm unsure if an employer would want to hire someone for 4 months of part-time work). That said, it seems--based on the advice of people who have experienced law school before--best to take the time to find out how much time you have, and how you deal with the commitments and rigours of 1L, before you lock yourself into a position.

In short, yes. Did you have any correspondence at all with them? I had a similar "issue" (or so I thought), but was able to get one very good reference from a professor I didn't really "know" all that well. Professors are generally very interested in helping out--this particular professor actually offered to help edit my personal statement and gave me a few pointers in the end. It can be kind of stressful at first, but many professors will simply ask the usual questions: Why do you want to go to law school? What do you see yourself doing with a law degree? Et cetera. Some will ask you to send them work you did in the class (if that's applicable/possible--I was never a science major, so I don't know).
Honestly, the worst thing they could possibly say is "sorry, I don't feel comfortable writing you a letter of reference", but the likelihood of that happening is small. They're likely asked for something of the sort all the time, and they should be able to glean some sort of meaningful insight as to what kind of student you were/are based on previous work and their class records. Be honest and genuine in your request as well as your answers to their questions, and I don't see an issue there. Augment that with a very good professional reference, and you're well on your way.

Directly from U of C Law's admissions website:
It appears as though they want at least one, but advise two academic references. In practice, using one phenomenal professional reference instead of a mediocre second academic reference seems obviously preferable.
Your GPA appears a bit on the low side, but depending on your EC's, professional experience, LORs, and how strong your personal statement is, you still have a chance. Aim for mid- to high-160s on the LSAT, and your chances increase significantly.

I didn't drop off my package in person, but I had my mailed-in acceptance package tracked so I know exactly when it was received. It took about a week to get the confirmation of receipt and processing.

That's an incredibly common-place feeling, I imagine. Truth is though, they're your parents. I doubt your "success" (however you perceive that), is as important to them as your happiness. You seem like you're asking the correct questions--which is more than most (certainly more than I ever did).
At the risk of totally derailing this thread (before it even starts); yes, in a sense. I would suggest you not wait until you've had that first poor mark, and don't go in unprepared. Know exactly what you want to talk about. Know the questions you want to ask. Have as much knowledge about what you're discussing as you possibly can, even if you don't comprehend it fully. Professors are far more likely to: 1) acknowledge that you've put work in (which they like, and are thus more likely to help you), and 2) remember who you are (for any potential letters of reference or Master's degree work in the future).

This isn't at all answering your questions per se, but if I have one piece of advice, it would be: enjoy yourself. By all means, get a good GPA, do your extra-curriculars, work hard, develop good academic habits, and have fun--the latter is not mutually exclusive from any of the former. You will change a lot in 4 years. That's part of life. You might discover something you have no idea at this particular epoch that you absolutely love.
Sure, upon self-reflection, there were times I wish I had hunkered-down a bit more during my undergraduate degree, but that's also kind of part-and-parcel of the whole experience--I don't foresee any 40 year-old tent-dwelling in my future. That said, I'm not coming from the "perfect potential law-student" perspective. I am, after all, a 0L for this upcoming September after finally being admitted. I've been out of my undergrad for a reasonable amount of time. Would I necessarily change the way things went for me? Not at all.
Seriously, enjoy your undergrad. The (proverbial) shit starts to hit the fan a lot sooner than you'd like to believe fresh out of highschool (or late-teens, whatever...)--those four years fly by. Be serious about your work, but as with most things, it's all about balance.
Also, as a tangential piece of practical advice: go to office hours. Professors are scary, but the vast majority are ridiculously helpful. That's one thing I wish I realised sooner.